# US 2018/0026201 A1 · Carbazole-based gumbos for highly efficient blue oleds

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- Number: US 2018/0026201 A1
- Document ID: US20180026201A1
- Status: Published application
- Kind: A1
- Application number: 15/541,524
- Filed: 2016-01-05
- Published: 2018-01-25
- Earliest claimed: 2015-01-05
- Assignees: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
- Applicants: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
- Inventors: NOUREEN SIRAJ; ISIAH MANUEL WARNER; THENAHANDI PRASANTHI DEEPTHIKA DE SILVA
- Web page: https://patentgrep.com/patent/US20180026201A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07C 303/30: by reactions not involving the formation of esterified sulfo groups
- C07C 303/40: by reactions not involving the formation of sulfonamide groups
- C07C 309/66: Methanesulfonates
- C07C 311/48: having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/14: containing three or more hetero rings
- H01G 9/2013: {the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- H10K 50/135: comprising mobile ions
- H10K 50/16: Electron transporting layers
- H10K 71/311: {Purifying organic semiconductor materials}
- Y02E 10/542: Dye sensitized solar cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H01G: CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE (selection of specified materials as dielectric H01B3/00; capacitors having potential barriers H10D1/62, H10K10/10)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Various examples are provided for carbazole-based GUMBOS (group of uniform materials based on organic salts), and its application in organic light emitting diodes (OLEDs). In one example, a composition includes a solid phase carbazole-based GUMBOS (group of uniform materials based on organic salts) comprising a counterion such as, e.g., trifluoromethanesulfonate ([Otf]), bis-(trifluoromethanesulfonyl)imide ([NTf2]), bis-(pentafluoroethylsulfonyl)imide ([BETI]), tetrafluoroborate (BF4), hexa-fluorophosphate (PF6), and/or thiocyanate (SCN). The carbazole-based GUMBOS can include carbazoleimidazole-based GUMBOS or 3,6-diBDC carbazolium-based GUMBOS. In another example, a method includes preparing a biphasic solution; separating a layer of DCM from the biphasic solution after stirring; washing the DCM with water to remove byproducts; and evaporating the DCM to form a solid phase carbazoleimidazole-based GUMBOS. Preparing the biphasic solution can include carbazoleimidazolium iodide (CM) dissolved in dichloromethane (DCM) and a dissolved salt including a sodium salt or a lithium salt.

## Claims

### Claim 1

A composition, comprising:
a solid phase carbazole-based GUMBOS (group of uniform materials based on organic salts) comprising a carbazole-based counterion.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the carbazole-based counterion is selected from the group consisting of trifluoromethanesulfonate ([OTf]), bis-(trifluoromethanesulfonyl)imide ([NTf2]), bis-(pentafluoroethylsulfonyl)imide ([BETI]), tetrafluoroborate (BF4), hexafluorophosphate (PF6), and thiocyanate (SCN).

### Claim 3 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS comprises an imidazole group or (alkyl)imidazole group at a 3-, 6-, or N-position of a carbazole unit.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the (alkyl)imidazole group is a (methyl) imidazole group at the 3-position of the carbazole unit.

### Claim 5 (depends on 3)

The composition of claim 3, wherein the imidazole group is at the 3 position of the carbazole unit.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS has a fluorescence quantum yield of about 73% or greater.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the carbazole-based GUMBOS has a fluorescence quantum yield of about 94% or greater.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the carbazole-based GUMBOS has a fluorescence quantum yield of about 99% or greater.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS has a thermal decomposition temperature (Td) in a range from about 350° C. to about 450° C.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS comprises carbazoleimidazolium trifluoromethanesulfonate [Cl][OTf], carbazoleimidazolium bis-(trifluoromethylsulfonyl)imide [Cl][NTf2], or carbazoleimidazolium bis(pentafluoroethylsulfonyl)imide [Cl][BETI].

### Claim 11 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS comprises 3,6-diBDC carbazolium trifluoromethanesulfonate [BDCC OTf], 3,6-diBDC carbazolium bis-(trifluoromethylsulfonyl)imide [BDCC NTf2], or 3,6-diBDC carbazolium bis(pentafluoroethylsulfonyl)imide [BDCC BETI].

### Claim 12 (depends on 1)

The composition of claim 1, wherein the carbazole-based GUMBOS exhibits radiative emission from a second excited singlet state.

### Claim 13 (depends on 12)

The composition of claim 12, wherein the carbazole-based GUMBOS further exhibits radiative emission from a first excited singlet state.

### Claim 14 (depends on 12)

The composition of claim 12, wherein an energy gap between a first excited singlet state of the carbazole-based GUMBOS and the second excited singlet state is greater than 6000 cm−1.

### Claim 15 (depends on 1)

An organic light emitting diode (OLED), comprising an active layer including the carbazole-based GUMBOS of claim 1.

### Claim 16 (depends on 15)

The OLED of claim 15, wherein the active layer is disposed between a first electrode and a second electrode.

### Claim 17 (depends on 16)

The OLED of claim 16, wherein the active layer comprises a GUMBOS emission layer and an electron transport layer.

### Claim 18

A method, comprising:
preparing a biphasic solution comprising carbazoleimidazolium iodide (ClI) dissolved in dichloromethane (DCM) and a dissolved salt comprising a sodium salt or a lithium salt;
separating a layer of DCM from the biphasic solution after stirring;
washing the DCM with water to remove byproducts; and
evaporating the DCM to form a solid phase carbazoleimidazole-based GUMBOS (group of uniform materials based on organic salts).

### Claim 19 (depends on 18)

The method of claim 18, wherein the dissolved salt comprises sodium trifluoromethanesulfonate (NaOTf) dissolved in deionized water.

### Claim 20 (depends on 19)

The method of claim 19, wherein the carbazoleimidazole-based GUMBOS comprises carbazoleimidazolium trifluoromethanesulfonate [Cl][OTf].

### Claim 21 (depends on 18)

The method of claim 18, wherein the dissolved salt comprises lithium bis(trifluoromethylsulfonyl)imide (LiNTf2) or lithium bis-(pentafluoroethylsulfonyl)imide (LiBETI) dissolved in deionized water.

### Claim 22 (depends on 21)

The method of claim 21, wherein the carbazoleimidazole-based GUMBOS comprises carbazoleimidazolium bis-(trifluoromethylsulfonyl)imide [Cl][NTf2] or carbazoleimidazolium bis(pentafluoroethylsulfonyl)imide [Cl][BETI].

### Claim 23 (depends on 18)

The method of claim 18, wherein the carbazoleimidazole-based GUMBOS is based upon anion exchange of N-Ethylhexyl-3-imidazolium carbazole.

### Claim 24 (depends on 18)

The method of claim 18, wherein the biphasic solution was stirred for 3-4 days.

### Claim 25 (depends on 18)

The method of claim 18, further comprising freeze drying the carbazoleimidazole-based GUMBOS.